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12 Great Pickup Lines for Older Women Working in 2023

You can use pickup lines for older women on someone as hot as her

Are you looking for the best pickup lines for older women? If so, you are in the right place to learn some magic words to get her number or in your bed.

There’s plenty of great advice on how to pick up younger women or shy women, but dating older women can be a mystery for some men. However, with the right pickup lines for older women, you might end up getting a laugh or impressing the mature lady of your choice.

This article is a list of pickup lines for attracting older women whether online or in real life. We’ll take an in-depth look at why these pickup lines work and whether each line is better for use online or in person.

Pickup Lines for Older Women That Work

Before we get into the best pickup lines for older women, it’s important to have a bit of context on why these lines are similar or different from pick-up lines that you’d use on younger women.

In our contemporary society, an older woman is simply a woman that has aged out of the designation of a “young woman”. Because women naturally mature faster and are faced with society’s delineations of what constitutes “young” and “old” this distinction is typically designated in the western world at age 35 or older.

Obviously, men wishing to date older women should be aware that older women respond differently to different pickup lines. Older women have seen all of the different tactics that men use since they’ve become attractive to men, but often have a better sense of humor from years of experience. This means that you are able to try out pickup lines that are more bold, bawdy, and tantalizing than you would with an inexperienced woman.

Now that we’ve got that basic understanding out of the way, let’s take a look at some pickup lines that you can use on women over 35. We’ll also point out which pickup lines work in-person or online.

Dating Apps Coaches Recommend to Meet Older Women

Most older women are meeting guys online now, many ONLY look online. It's also the best place to practice these lines. There are a lot of apps out there but not many are great for meeting single older women. These are the best options right now that consistently work for regular guys:

SiteOur ExperienceOur RatingFree Trial Link
Best For Relationships
Experience Highlights
Experience Highlights
  • Easily the best option for long-term relationships
  • 75% of all online marriages start here
  • 70% of users meet their spouse within a year
  • In-depth signup and matching process
Try eHarmony
Best For Casual Fun
Experience Highlights
Experience Highlights
  • The best way to meet women for casual relationships
  • Best results for regular guys
  • Over 60 million active members
  • Not good for long-term relationships
Try AFF For Free
Decent For Younger Guys
Cougar Life Highlights
Cougar Life Highlights
  • Focused on younger men meeting older women
  • A mix of relationships and hookups
  • Growing
  • Not as popular as eHarmony of AFF
Try Cougar Life

“I can get a great discount on those pants you are wearing. They’re 100% off at my place.”

Older woman at the office

This pickup line works for older women because what woman doesn’t love a deal? Plus, it showcases some great wordplay that clearly states your intention of fun times in the bedroom

Online or in-person? This pickup line obviously works well in person (if she’s wearing pants). For online flirting, this can be a great pickup line if she sends you a picture.

“Geez, you are so beautiful you made me forget my pickup line!”

Older women are typically more forgiving than younger women, so using a line that has a bit of plausible deniability (you may have actually forgotten your pickup line) and uses some flattery is a great move.

Online or in-person? This pickup line works for in-person encounters, but you can use variations for online texting. For example, “Hey, I had something witty and flattering to send to you, but your beauty gave me amnesia!”

New course

Can I get you anything? A soda, a drink, a wedding ring?

If she’s an older woman, there’s a good chance she’s been married or wants to get married. By slipping it in there among the normal things men offer women at a bar, you can elicit laughter at the absurdity of the question. Plus, this pickup line follows the Rule of 3, a key element of comedy.

Online or in-person? This is primarily an in-person pick up line. However, you can use the Rule of 3 in other online banter. For example, you may be talking about what you want out of life and respond, “I’m looking for new experiences, happiness, and your lips on mine.”

“I’m no organ donor, but I’d gladly give you my heart.”

Hot older woman on the phone

Women love cutesy pickup lines like this that have a bit of a romantic undertone. And because women in their later years are often starved for romance, offering love might make her take you a bit more seriously than a jokey line.

Online or in-person? Both. Though we suggest avoiding this line if you’re on a hookup app.

Cougar Pickup Lines

Okay, now that we’ve covered great pickup lines for older women, you should know that there are other pickup lines that you can use on cougars. A cougar is an older woman looking for a sexual relationship with a younger man. Because women in their later years tend to have higher levels of sex hormones, they love to find younger men that will fulfill their desires.

The key to approaching cougars on Tinder and different dating apps is to have a unique pick-up line that gets down to business: sex and lots of it. You can be witty and interesting, but cougars usually want to seal the deal and get down to business ASAP.

Confidence also goes a long way when seducing cougars with pickup lines. Summoning the courage to approach her and nailing a pickup line usually will at least get her to entertain your presence. If you are lucky, you might even be heading to your place or hers quicker than the time it took you to say the line!

Let’s take a look at a few cougar pickup lines to use on a woman who's much older than you but are looking for a good time, plus whether they work better online or in-person.

“If being sexy was a crime, you’d be guilty as charged.”

One of the reasons why picking up cougars is such fun is that they’re a bit of a taboo. Our society tends to shy away from the sexual desires of women as almost something criminal. So, why not play that up a little bit?

Online or in-person? Both. In person, you can add “Ma’am, please put your hands behind your back so I can restrain you.” as an added tag to hint at tying her up later at your place or hers.

“I think you are a squirrel because I think you can help me bust a nut.”

Squirrels are cute and fun animals, so you won’t offend a cougar that enjoys a bit of coded language.

Online or in-person? Both.

H apps promo

“Nice shoes. Wanna f*ck?”

Talk about getting to the point!

Online or in-person? Works in-person, but you can throw this as non-sequitur if you want to seal the deal.

“Kiss me if I’m wrong but, dinosaurs still exist, don’t they?”

If you are looking to make out with a cougar sooner than later, why not create a pickup line that puts it out there with a bit of absurdity? Feel free to modify this line as you see fit, replacing “dinosaurs still exist” with another obviously wrong statement.

Online or in-person? This is primarily an in-person line, but you can use a variation like “You owe me a kiss if I’m wrong, but dinosaurs still exist, right?”

Pick up lines for MILFs

Thanks to the popular film American Pie, the term MILF (Mom I’d Like to Fuck) has entered into popular lexicon. And with it are older mothers that are looking for a good time.

Just like cougars, MILFs are sex-savvy and experienced (obviously), but it’s fun to remind them that they’re still attractive and haven’t completely turned into matrons as they age.

The following are a few great pickup lines that you can use on MILFs in-person or online.

“Is your name ‘homework’ because I’m not doing you and I should be”

An older woman giggling as you use a pickup line

If she’s got children, she knows all about getting her kids to do homework. Play into this dynamic with a bit of wordplay. Feel free to add other tags, such as “What grade would you give that pickup line, Ms. Teacher?” or “Uh oh, I might have to make up some time after class for that line…”

“Aside from taking my breath away, what do you do for a living?”

If she’s a hot momma, chances are that she’s working. The best part of this pickup line is that you can segue into other types of conversation to either get her number, make her laugh, or make some plans to fit you in her “schedule” (wink wink).

H apps promo

You look so hot my air-conditioning bill is going up

Moms usually pay the utility bills, so use this line to make her feel a little guilty for costing you a little extra this month. Just don’t forget to turn off the lights when you are done using them!

“I like my women the same way I like my alcohol: Aged to perfection.”

Women don’t like to talk about their age, but they certainly like being enjoyed for their refined sensibilities and sophistication. Suggesting that she’s a perfect libation for your enjoyment is sure to make her toes curl and get her heart racing!

Online or in-person? Both. When you use this in-person, you can smoothly segue to a “Can I buy you a drink?” line to steal a little of her time for yourself.


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